US5011611A - Method of separation of furfural from diluted aqueous solutions - Google Patents

Method of separation of furfural from diluted aqueous solutions Download PDF

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Publication number
US5011611A
US5011611A US07/452,269 US45226989A US5011611A US 5011611 A US5011611 A US 5011611A US 45226989 A US45226989 A US 45226989A US 5011611 A US5011611 A US 5011611A
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US
United States
Prior art keywords
furfural
separation
adsorbent
aqueous solutions
diluted aqueous
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US07/452,269
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English (en)
Inventor
Karel Jerabek
Karel Setinek
Frantisek Kastanek
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Czech Academy of Sciences CAS
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Czech Academy of Sciences CAS
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Assigned to CESKOSLOVENSKA AKADEMIE VED reassignment CESKOSLOVENSKA AKADEMIE VED ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: JERABEK, KAREL, KASTANEK, FRANTISEK, SETINEK, KAREL
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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D15/00Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds
    • B01J20/261Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds
    • B01J20/265Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267Cross-linked polymers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48Furfural
    • C07D307/50Preparation from natural products

Definitions

  • the invention concerns the method of separation of furfural from diluted aqueous solutions.
  • Furfural is manufactured by acid hydrolysis of plant residues. This process produces diluted aqueous solutions in which furfural is contained in concentration as low as 1%. Common methods of furfural separation from these solutions are distillation and extraction by suitable solvents. (Encyklopedia of Chemical Procesing and Design, Marcel Dekker Inc., vol. 24, p. 53, New York 1986) Both methods have serious disadvantages. Distillation of aqueous furfural solutions is complicated by the formation of the azeotrope which at the atmospheric pressure contains approx. 36% of furfural. After condensation the azeotrope separates into two layers, the aqueous one is recirculated and from the remaining one liquid pure furfural is obtained in the second distillation step.
  • the first distillation step is possible to replace by extraction using a suitable solvent immiscible with water. In this case, the complications are caused by traces of the extracting solvent in waste waters.
  • the present invention relates to the process in which furfural is separated from its aqueous solutions using a bed of chemically inert polymer adsorbent.
  • the polymer adsorbent is a porous copolymer of styrene and its derivatives with surface area higher than 30 m 2 /g from which furfural is subsequently desorbed by an alcohol with 1-3 carbon atoms.
  • the polymer acts as a heterogenized extraction agent whose affinity toward furfural molecules is much higher than the affinity of water molecules.
  • the bed of polymer adsorbent saturated by furfural is possible to regenerate by a solvent in which furfural is substantially better soluble than in water but which has small affinity toward the polymer, that is, a solvent in which the polymer does not swell.
  • a solvent in which the polymer does not swell for this purpose alcohols with 1-3 carbon atoms are suitable.
  • furfural was contained in concentration at least ten times higher than had been its concentration in original aqueous solution.
  • the separation of furfural from alcoholic solution by adsorption separation is not complicated by the azeotrope formation and due to the low heat of vaporization of the alcohol, it is less energy-demanding than the distillation of aqueous solutions.
  • the solvent used for the adsorbent regeneration can be recirculated.
  • the adsorptive separation according to present invention is substantially more energy-efficient. This new process is also able to separate furfural from very diluted solutions containing less than 1% of furfural for which traditional methods using distillation or extraction are quite unsuitable.
  • an adsorbent having the BET surface area 750 m 2 /g was prepared by the method of crosslinking in swollen state described in DDR Pat. No. DD 249,274.
  • first traces of furfural in the eluate were observed after passing of 210 cm of 1% aqueous furfural solution through the column.
  • furfural was desorbed from the column in 33 cm 3 of n-propanol.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
US07/452,269 1988-12-16 1989-12-15 Method of separation of furfural from diluted aqueous solutions Expired - Fee Related US5011611A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CS888371A CS271942B1 (en) 1988-12-16 1988-12-16 Method of furfural insulation from diluted aqueous solutions
CS8371-88 1988-12-16

Publications (1)

Publication Number Publication Date
US5011611A true US5011611A (en) 1991-04-30

Family

ID=5434171

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/452,269 Expired - Fee Related US5011611A (en) 1988-12-16 1989-12-15 Method of separation of furfural from diluted aqueous solutions

Country Status (6)

Country Link
US (1) US5011611A (cs)
CA (1) CA2005632A1 (cs)
CS (1) CS271942B1 (cs)
DE (1) DE3941528A1 (cs)
FI (1) FI896023A7 (cs)
SE (1) SE8904232L (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6409889B1 (en) 1999-04-13 2002-06-25 Special Materials Research And Technology, Inc. Method for the removal and recovery of inorganic pollutants from waste aqueous solutions and waste primary air sources

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4417081C2 (de) * 1994-05-17 1998-03-12 Chmiel Horst Verfahren zur Entfernung organischer Verbindungen aus Fluiden

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531463A (en) * 1965-02-24 1970-09-29 Rohm & Haas Enrichment and/or separation of an organic compound by adsorption processes
US4071398A (en) * 1975-06-18 1978-01-31 Flambeau Paper Company Chemical concentration by sequential activated carbon adsorption and fractionation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531463A (en) * 1965-02-24 1970-09-29 Rohm & Haas Enrichment and/or separation of an organic compound by adsorption processes
US4071398A (en) * 1975-06-18 1978-01-31 Flambeau Paper Company Chemical concentration by sequential activated carbon adsorption and fractionation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6409889B1 (en) 1999-04-13 2002-06-25 Special Materials Research And Technology, Inc. Method for the removal and recovery of inorganic pollutants from waste aqueous solutions and waste primary air sources

Also Published As

Publication number Publication date
FI896023A0 (fi) 1989-12-15
SE8904232D0 (sv) 1989-12-15
CS837188A1 (en) 1990-03-14
SE8904232L (sv) 1990-06-17
CS271942B1 (en) 1990-12-13
DE3941528A1 (de) 1990-06-21
FI896023A7 (fi) 1990-06-17
CA2005632A1 (en) 1990-06-16

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Legal Events

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AS Assignment

Owner name: CESKOSLOVENSKA AKADEMIE VED, CZECHOSLOVAKIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:JERABEK, KAREL;SETINEK, KAREL;KASTANEK, FRANTISEK;REEL/FRAME:005244/0779

Effective date: 19891207

REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
FP Lapsed due to failure to pay maintenance fee

Effective date: 19950503

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362